((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol

Base Information

• Chemical Name: ((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol
• CAS No.: 1313511-88-4
• Molecular Formula: C₃₀H₅₆O₆Si₂
• Molecular Weight: 568.942
• Mol file: 1313511-88-4.mol

Synonyms:((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol

Chemical Property of ((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol

There total 26 articles about ((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

C30H56O5Si2 → ((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol (1313511-88-4)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; In decane; dichloromethane; at -23 ℃; for 12.75h; Temperature; Inert atmosphere; Molecular sieve;

DOI:10.1002/asia.201402593

Reference yield:

(5S,6S,8R,E)-6,9-bis((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-8-methylnon-2-en-1-ol (1313511-87-3) → ((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol (1313511-88-4)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; In dichloromethane; toluene; at -20 ℃; for 12h; optical yield given as %de; stereoselective reaction; Molecular sieve;

DOI:10.1039/c0ob01253j

Reference yield:

C17H23NO4 → ((2S,3S)-3-((2S,3S,5R)-3,6-bis((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)-5-methylhexyl)oxiran-2-yl)methanol (1313511-88-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: sodium tetrahydroborate / ethanol; water; dimethyl sulfoxide / 0.5 h / 20 °C

2.1: acetic acid; zinc / ethanol / 2 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C

4.1: camphor-10-sulfonic acid / dichloromethane / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

7.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 0.5 h / 0 °C

8.1: 1,1'-carbonyldiimidazole / dichloromethane / 0 °C

9.1: tert.-butyl lithium / diethyl ether; pentane / 0.25 h / -78 °C

9.2: -78 °C

10.1: L-Selectride / tetrahydrofuran / 1 h / -78 °C

11.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C

12.1: magnesium bromide ethyl etherate / diethyl ether / 2 h / 20 °C

13.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dichloromethane; toluene / 12 h / -20 °C / Molecular sieve

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tert.-butyl lithium; sulfur trioxide pyridine complex; L-Selectride; magnesium bromide ethyl etherate; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; zinc; In tetrahydrofuran; 2-methyl-but-2-ene; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; pentane; 6.1: Parikh-Doering oxidation / 13.1: Sharpless asymmetric epoxidation reaction;

DOI:10.1039/c0ob01253j

upstream raw materials:

(2S,E)-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-4-ene-1,2-diol

C₁₇H₃₄O₄Si

(2S,E)-2-((4-methoxybenzyl)oxy)-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-4-en-1-ol

C₁₉H₂₆O₆

Downstream raw materials:

(5S,7R)-5-((S)-1-((4-methoxybenzyl)oxy)-2-((2R,3S)-3-vinyloxiran-2-yl)ethyl)-2,2,3,3,7,10,10,11,11-nonamethyl-4,9-dioxa-3,10-disiladodecane

Refernces

• 1、 Zhang, Yao,Deng, Lisheng,Zhao, Gang. "A stereoselective total synthesis of 7,8-O-isopropylidene iriomoteolide-3a". . p. 4518 - 4526. Retrieved 2011/07/29.